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Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent “Click-Declick” Chemistry Full article

Journal Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263
Output data Year: 2018, Volume: 83, Number: 17, Pages: 9756-9773 Pages count : 18 DOI: 10.1021/acs.joc.8b01296
Authors Golovanov Ivan S. 1 , Mazeina Galina S. 1,2 , Nelyubina Yulia V. 3 , Novikov Roman A. 1 , Mazur Anton S. 4 , Britvin Sergey N. 5 , Tartakovsky Vladimir A. 1 , Ioffe Sema L. 1 , Sukhorukov Alexey Yu. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow 119991, Russia
2 Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, Moscow 125047, Russia
3 A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilov Str. 28, Moscow 119991, Russia
4 Center for Magnetic Resonance, St. Petersburg State University, University Av. 26, St. Petersburg 198504, Russia
5 Department of Crystallography, St. Petersburg State University, Universitetskaya Nab. 7/9, St. Petersburg 199034, Russia

Abstract: Click-like condensation of boronic acids with specifically designed triols (boronate-triol coupling) produces stable diamantane adducts in aqueous medium, which can be controllably cleaved to initial components under acidic conditions or by using boric acid as a chemical trigger. This novel “click-declick” strategy allows for the creation of temporary covalent connections between two or more modular units, which was demonstrated by the synthesis of new fluorophore-labeled natural molecules (peptides, steroids), supramolecular assemblies, modified polymers, boronic acid scavengers, solid-supported organocatalysts, biodegradable COF-like materials, and dynamic combinatorial libraries.
Cite: Golovanov I.S. , Mazeina G.S. , Nelyubina Y.V. , Novikov R.A. , Mazur A.S. , Britvin S.N. , Tartakovsky V.A. , Ioffe S.L. , Sukhorukov A.Y.
Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent “Click-Declick” Chemistry
Journal of Organic Chemistry. 2018. V.83. N17. P.9756-9773. DOI: 10.1021/acs.joc.8b01296 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000444364600016
Scopus: 2-s2.0-85052327261
OpenAlex: W2886965895
Citing:
DB Citing
OpenAlex 30
Scopus 22
Web of science 22
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